Author: Shira Abel Category: Enterprise Marketing URL: https://hunterandbard.com/resources/blog/the-18-month-tax
Spending $10,000 on <a href="/resources/blog/what-messaging-and-positioning-can-and-cannot-do" class="text-[#316263] font-bold underline">messaging</a> feels reckless when your runway is short. But the real tax isn't the consultant fee. It’s the 18 months of high-friction sales and muddied feedback that follow. You aren't saving money; you're paying for the privilege of moving slower. Here is why getting your story right is the highest ROI move you can make for your sales velocity.
Founders who skip outside expertise pay what amounts to an 18-month trial-and-error tax: 780+ hours of beginner-level work worth $156K+, delayed sales learning curves, and burned runway. Data from BLS, CB Insights, and Harvard Business School research all confirm that missing expertise, not missing capital, is what kills startups in years two through five. Fractional CMOs, contract counsel, and part-time specialists cost a fraction of the DIY alternative. Wasting time is expensive.
I get it. I really do.
When you're staring at a runway that feels shorter every month, spending $10,000 on a consultant feels reckless. You didn't build something from nothing to hand it off to someone else. You're smart. You can figure it out. And besides, what if it doesn't work? What if you spend the money and still don't get traction?
That fear is legitimate. I've felt it. Most founders I know have felt it. But here's what I've watched happen, over and over, to people who let that fear make their decisions for them: they end up spending far more than the expert would have cost. They just spend it slower, in ways that are harder to see on a spreadsheet, and by the time they realize it, 18 months have evaporated. And it's cost them far more than the cost of the expert in the first place.
I call it the trial-and-error tax. And the data backs it up.
The U.S. Bureau of Labor Statistics tracks business survival rates with the kind of cold accuracy that doesn't care about your pitch deck. About 20% of new businesses fail within year one. That's not the alarming part. The alarming part is what happens next. The highest-risk window isn't the first year, when you're still running on adrenaline and the idea is new. It's years two through five, when the early momentum fades, funding gets thin, and you actually have to prove the business can sell. Nearly half of all startups are gone by year five.
CB Insights dug into the why by analyzing over 400 VC-backed startups that shut down. These weren't underfunded ideas. Together, the companies they studied had raised over $17.5 billion before dying. The median company raised $11 million. Money wasn't the issue. The top killers were no real product-market fit (42% of failures), running out of cash (29%), and not having the right team around them (23%).
That last one is the one nobody wants to talk about honestly.
When researchers say 23% of startups fail because of team issues, most founders read that as co-founder conflict or a bad hire. Sometimes it is. But more often, it means the founding team was missing the expertise they needed and either didn't recognize the gap or couldn't bring themselves to pay to fill it.
Tom Eisenmann, a professor at Harvard Business School who spent years studying why startups fail across 470 companies, identified what he calls the "Help Wanted" failure pattern. A team that lacks the skills the business needs at a critical moment and moves too slowly to fix it. His research is pretty unambiguous: you can't study your way out of this gap fast enough. The market doesn't pause while you take the course.
And yet, founders keep trying. Because the alternative feels like a gamble. Because expertise costs money up front, and mistakes feel like they cost nothing. Until you add them all up.
Here's where the trial-and-error tax gets really expensive, and it's the piece I don't see enough founders take seriously.
Every month you're spending 15 hours a week trying to teach yourself SEO, rewriting your own copy for the fourth time, or figuring out whether your contract is enforceable — that's time you are not spending on sales. Not just in the hours-in-a-day sense. You're also not building the deep market knowledge that makes sales possible at scale.
Mark Leslie and Charles Holloway wrote about this in Harvard Business Review back in 2006, and it's still one of the most useful frameworks I know. They called it the Sales Learning Curve, the idea that every organization has to accumulate real selling knowledge before it can generate predictable revenue. You can't skip ahead on that curve. You earn your place on it through actual sales conversations, real feedback, real losses. The problem is that every month you're not having those conversations, you're falling further behind.
The typical sales rep takes about 180 days to ramp to full productivity. But before you can even hire effectively, you need to know what a good sale looks like in your business. Founders who spend the first year and a half building skills they should have outsourced are delaying that discovery. And by the time they get there, they've burned runway and time they can't get back.
I want you to do something uncomfortable. Think about the hours you've spent in the last 18 months on tasks outside your actual expertise. Writing copy. Figuring out your tax structure. Teaching yourself Facebook ads. Building a sales process from scratch with no model to reference.
If it's even 10 hours a week, that's 780 hours over 18 months. If your time is worth $200 an hour, and if your startup is viable, it is worth at least that, you've invested $156,000 in activities you're doing at a beginner level. The consultant you passed on because they charged $8,000? You've already spent more than that twenty times over, just in your own time. And that's before you factor in the revenue you didn't close while you were busy figuring out what everyone else on your team already knows.
The Kauffman Foundation, which tracks entrepreneurship data nationally, has found consistently that access to the right expertise, not just capital, is one of the biggest predictors of whether a startup survives past year five. Founders who rely entirely on personal problem-solving in areas outside their core competency are the most financially exposed when growth transitions get hard.
I'm not writing this to make you feel bad about decisions you've already made. I'm writing it because I've sat across from too many founders who, twelve or eighteen months in, say some version of the same thing: I wish I'd called you sooner. I thought I couldn't afford it, but it turns out I couldn't afford not to.
The fear that drives the DIY decision isn't irrational. You're protecting something you built. You don't know if it's going to work. Spending money on experts when you're not yet profitable feels like a bet you're not sure you can make. I understand that completely.
But the decision isn't "expert cost versus zero." The actual comparison is expert cost versus the total bill of the trial-and-error tax, and that bill, once you add it up honestly, almost never comes out in favor of going it alone.
You don't have to hire full-time. The market for fractional expertise is wide open right now. Fractional CMOs, contract legal counsel, part-time sales directors who've built what you're building before, none of these require a six-figure salary line. They require a willingness to admit that your time, and your growth, is worth protecting.
Start with wherever your biggest unknown is. Not the thing you've been avoiding because it's hard. The thing you've been avoiding because you're not sure what good even looks like. That's almost always where the tax is highest.
The expert isn't the luxury. The 18 months of figuring it out yourself is.
Hunter & Bard is a San Francisco-based B2B strategy consultancy founded in 2011 by Shira Abel. We help deep-tech and enterprise SaaS companies fix their positioning, sharpen their messaging, and close $100K+ deals.
We work with B2B leaders who are tired of being overlooked, underestimated, or mistaken for their competitors. Our specialty is turning complex, technical products into clear, compelling stories that win enterprise deals.
We believe that perception drives revenue. If your buyers can't tell you apart from the next vendor in 30 seconds, you have a positioning problem — not a marketing problem. We fix that.
Perception = (Story × Visibility) ÷ Noise
This framework drives everything we do. Your story has to be sharp. Your visibility has to be strategic. And you have to cut through the noise — not add to it.
Shira Abel — Founder & CEO. Kellogg MBA. 20+ years in B2B marketing. Former CMO. Keynote speaker. Published in Forbes, HuffPost, and Wired. Specialist in enterprise positioning and perception strategy.
Daina Reed — Founding Designer & Partner. 15+ years in product and brand design. Former Senior Product Designer at Dun & Bradstreet. Specialist in enterprise UX, visual identity, and design systems.